Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

• Tatsuhiro Uchikura,
• Nanami Kamiyama,
• Taisuke Ishikawa and
• Takahiko Akiyama

Beilstein J. Org. Chem. 2020, 16, 2442–2447, doi:10.3762/bjoc.16.198

• -trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)–CF3 species is the rate-determining step. Keywords: benzimidazoline

• recently reported the trifluoromethylation of iodoarenes by use of 2-aryl-2-trifluoromethylbenzimidazoline as the trifluoromethylating reagent in the presence of 3 equiv of a copper salt [22]. The benzimidazoline derivatives could be readily prepared from relatively cheap materials, namely

• , trifluoromethylacetophenone and phenylenediamine derivatives (Figure 1b). Herein we report a catalytic trifluoromethylation of iodoarenes by use of benzimidazoline derivatives in the presence of a catalytic amount of copper salts and a bipyridyl ligand (Figure 1c). Results and Discussion We first investigated the reaction

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• applied to 72d or a substrate similar to 72e. More recently, the reaction of dibenzylmalononitrile 72b with the hydroxyaryl-substituted benzimidazoline derivative 81 as photo-reductant in a basic medium has been described and led to 73b in fair yield (Scheme 27) [128]. Acid, base or organometallic-induced